Pyridine compounds which are useful as fungicides

ABSTRACT

Pyridines of the formula ##STR1## where R 1  is hydrogen, C 1  -C 6  -alkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkynyl or an acyl radical COR 2  ; R 2  is C 1  -C 6  -alkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkynyl, C 1  -C 6  -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR2## where R 3  and R 4  are identical or differ and each is C 1  -C 6  -alkyl, with the proviso that R 3  and R 4  are not simultaneously methyl; R 5  is one of the groups (CH 2 ) n , CH 2  OCH 2 , CH 2  S(O) m  CH 2 , CH 2  CH 2  O or CH 2  CH 2  S(O) m , n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is aryl which is unsubstituted or bears from one to five substituents selected from the group consisting of C 1  -C 6  -alkyl, phenyl, halogen, C 1  -C 6  -haloalkyl, C 1  -C 6  -alkoxy, C 1  -C 6  -haloalkoxy, C 1  -C 6  -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, and the N-oxides and plant-tolerated acid addition salts thereof, and fungicides containing these compounds.

The present invention relates to novel pyridine derivatives, the N-oxides and salts thereof, to a process for the preparation thereof and the use thereof for controlling fungi.

The novel pyridine derivatives have the formula ##STR3## where R¹ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl or COR² ;

R² is C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -haloalkyl or substituted or unsubstituted aryl;

A is ##STR4## R³ and R⁴ are, independently of one another, C₁ -C₆ -alkyl with the proviso that R³ and R⁴ are not both methyl;

R⁵ is (CH₂)_(n), CH₂ OCH₂, CH₂ S(O)_(m) CH₂, CH₂ CH₂ O, CH₂ CH₂ S(O)_(m) where

n is an integer from 1 to 5 and

m is an integer from 0 to 2;

Ar is aryl which carries 0-5 substituents from the group comprising C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminomethyl, phenoxy, halophenoxy and benzyloxy, and the N-oxides and the acid addition salts which are tolerated by plants of the pyridine compounds.

Examples of R¹ are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, n-hexyl; allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylallyl; propargyl.

Examples of R² are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentenyl, neo-pentyl, n-hexyl; trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromoethyl, 2-chloroethyl, 3-bromopropyl, 4-bromobutyl; aryl which carries zero to three substituents selected from the group comprising C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, cyano and nitro, such as naphthyl, phenyl, mono-, di- or trimethylphenyl, 4-tert-butyphenyl, mono-, di- or trimethoxyphenyl, trifluoromethylphenyl, fluorophenyl, mono-, di- or trichlorophenyl, mono- or dinitrophenyl and cyanophenyl.

Examples of R³ and R⁴ are, independently of one another, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and n-hexyl.

Examples of R⁵ are methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, oxydimethylene, ethyleneoxy, thiodimethylene, sulfinyldimethylene, sulfonyldimethylene, ethylenethio, ethylenesulfinyl and ethylenesulfonyl.

Examples of Ar are phenyl, naphthyl, indanyl, mono-, di-, tri- or tetramethylphenyl, ethylphenyl, propylphenyl, isopropylphenyl, butylphenyl, tert-butylphenyl, biphenylyl, methylnaphthyl, mono- or difluorophenyl, methylfluorophenyl, tri-, tetra- or pentafluorophenyl, fluorochlorophenyl, methylchlorophenyl, mono-, di-, tri-, tetra- or pentachlorophenyl, bromophenyl, fluorobromophenyl, mono- or bis-trifluoromethylphenyl, mono-, di- or trimethoxyphenyl, ethoxyphenyl, trifluoromethoxyphenyl, tetrafluoroethoxyphenyl, methoxyiminomethylphenyl, ethoxyiminomethylphenyl, phenoxyphenyl, fluorophenoxyphenyl, chlorophenoxyphenyl, chlorophenoxychlorophenyl and benzyloxyphenyl.

Preferred compounds of the formula 1 are those in which

R¹ is hydrogen, methyl, ethyl, tert-butyl, allyl, propargyl or COR²,

R² is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl or substituted or unsubstituted phenyl,

A is ##STR5## R³ and R⁴ are, independently of one another, methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl,

R⁵ is ethylene or 1,3-propylene, and Ar has the meanings specified in claim 1.

The present invention also relates to the N-oxides and the acid addition salts which are tolerated by plants of the novel pyridine derivatives. Examples of salts which are tolerated by plants of the pyridines are salts with mineral acids such as hydrochlorides, hydrobromides, sulfates, nitrates and phosphates; salts with alkanecarboxylic acids such as formates, acetates, propionates, 2-ethylhexanoates and oxalates; salts with arenesulfonic acids such as benzenesulfonates, toluenesulfonates and dodecylbenzenesulfonates.

The compounds of the formula 1 can contain two centers of asymmetry and thus exist in two diastereomeric forms which can be separated by conventional processes, for example by chromatography or crystallization. The present invention embraces both the individual diastereomers and the mixtures thereof and fungicides containing these compounds.

The compounds of the formula 1 have a good fungicidal action which is better than the action of conventional fungicides.

The use of pyridylcarbinols, e.g. 3-phenyl-2,2-dimethyl-1-(3-pyridyl)-1-propanol which is disclosed in EP 302 365, as fungicides has been disclosed. Their fungicidal action is, however, not always entirely satisfactory for certain indications, especially at low application rates.

The process for the preparation of the novel compounds of the formula 1 comprises an aldehyde of the formula 2

    Ar--CH.sub.2 --A--CHO                                      2

in which Ar and A have the meanings specified in claim 1, being reacted with an organometallic compound of the formula 3 ##STR6## in which M is lithium or MgCl, MgBr or MgI, and the resulting pyridyl alcohol of the formula 1 in which A and Ar have the meanings specified in claim 1, and R¹ is hydrogen, being either alkylated with a compound of the formula 4 or acylated with a compound of the formula 5 ##STR7## in which R¹ and R² have the meanings specified in claim 1 with the exception of hydrogen, and X and Y are nucleofugic groups.

Examples of X are chlorine, bromine, iodine, OSO₂ CH₃, OSO₂ C₆ H₅ and OSO₂ --C₆ H₄ --CH₃ (p).

Examples of Y are chlorine, bromine, iodine, ##STR8## or 1-imidazolyl.

The procedure for this reaction is such that, for example, a mixture of pyridyl alcohol of the formula 1 in which R¹ is hydrogen is introduced into at least the equimolar amount of an auxiliary base, with or without an inert organic solvent such as diethyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, acetonitrile, toluene or xylene, and then the alkylating or acylating agent is metered in.

The reaction is carried out at from 0° to 120° C., preferably 20° to 80° C., for example.

Auxiliary bases which can be used are inorganic and organic acid-binding agents.

Examples of inorganic bases are sodium hydride, sodamide, sodium hydroxide, sodium carbonate, potassium carbonate, potassium hydroxide etc.

Examples of organic bases are amines, especially tertiary amines such as triethylamine, ethyldiisopropylamine and pyridine, and alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate.

An occasionally advantageous variant of this process entails reacting the pyridyl alcohols of the formula 1 with alkylating agents of the formula 4 in a two-phase system composed of aqueous sodium hydroxide solution and an organic solvent, preferably toluene or dichloromethane, with the addition of a phase-transfer catalyst, eg. tetra-n-butylammonium chloride, benzyltriethylammonium chloride or methyltrioctylammonium chloride.

The novel pyridyl alcohols of the formula 1 in which R¹ is hydrogen can be prepared, for example, by reacting a metalated pyridine of the formula 3 in which M is lithium or MgCl, MgBr or MgI with an aldehyde of the formula 2 in which Ar and A have the meanings specified in claim 1, eg. in the presence of a suitable solvent.

This advantageously entails the organometallic compound of the formula 3 being introduced into an inert solvent, preferably an ether such as diethyl ether or tetrahydrofuran, at from -100° to +20° C., preferably from -70° to 0° C., and adding the aldehyde of the formula 2, which may be dissolved in a diluent, dropwise.

The metalated pyridines of the formula 3 are known and can be prepared from the corresponding 3-halopyridines (cf. e.g. N.Furukawa et al., Tetrahedron Letters 1987, 5845 for M=MgBr; A. Fischer and M. W. Morgan, J. Organomet. Chem. 136 (1977) 323 for M=Li).

Some of the aldehydes of the formula 2 are known, and they can be prepared by known processes by alkylating aldehydes of the formula 6 in which A has the meanings specified in claim 1 with a benzyl halide of the formula 7: ##STR9##

It is known that direct α-alkylation of aldehydes usually takes place with only poor yields; the same applies to the enamines derived from the aldehydes (cf. e.g. G. Opitz et al., Liebigs Ann. Chem. 649 (1961) 36). Better results are obtained when the aldehydes of the formula 6 are first converted into N-metalated imines which are then alkylated with benzyl halides (cf. H. Normant et al., Bull. Soc. Chim. Fr. 1970, 3976). A more straightforward method is phase-transfer catalyzed α-alkylation of aldehydes. This process can be carried out as the solid/liquid variant in a two-phase system composed of solid sodium hydroxide and a lipophilic organic solvent (cf. V. G. Poruhit and R. Subramanian, Chem. Ind. (London) 1978, 731) or as the liquid/liquid variant in a two-phase system composed of concentrated sodium hydroxide solution and a lipophilic organic solvent (cf. H. K. Dietl and K. C. Brannock, Tetrahedron Lett. 1973, 1273; E. Buschmann and B. Zeeh, Liebigs Ann. Chem. 1979, 1585).

Another process for the preparation of aldehydes of the formula 2 comprises alkylating nitriles of the formula 8 with benzyl halides of the formula 7, and converting the reaction products of the formula 9 with a suitable reducing agent into the aldehydes 2: ##STR10##

The α-alkylation of nitriles and the reduction of nitriles to aldehydes are known reactions (cf. e.g. D. S. Watt et al., Org. React. 31 (1984) 1 et seq.; M. Rabinovitz in Z. Rappoport (Ed.) "The Chemistry of the Cyano Group", pp. 307 et seq., Interscience, New York 1970; J. Malek and M. Cerny, Synthesis 1972, 217; N. M. Yoon and Y. S. Gyoung, J. Org. Chem. 50 (1985) 2443).

The aldehydes 6, nitriles 8 and benzyl halides 7 used as starting materials are known, and most of them are commercially available.

The examples which follow illustrate the preparation of the novel pyridine derivatives.

EXAMPLE 1 2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)butyl acetate (compound no. 611)

10.2 g (0.10 mol) of acetic anhydride are added dropwise to a solution of 12.1 g (0.04 mol) of 2-(4chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol in 50 ml of pyridine at room temperature, and the mixture is then heated at 80° C. for 8 h. The reaction mixture is concentrated, the residue is taken up in 200 ml of dichloromethane, and the solution is washed with saturated NaHCO₃ solution and then with water. The organic phase is dried and concentrated, and the remaining black oil is purified on silica gel (mobile phase: 5:1 cyclohexane/ethyl acetate). 11.2 g (81% of theory) of the title compound are obtained as a viscous yellow oil.

¹ H-NMR (CDCl₃): δ=8.60(2-Hpy), 8.52(6-Hpy), 7.65(4-Hpy), 7.30(5-Hpy), 7.25(2Hm), 7.05(2Ho), 5.62(CHOAc), 2.68(CH₂ Ar), 2.08(COCH₃), 1.45(CH₂), 1.30(CH₂), 0.95(CH₃), 0.83(CH₃).

EXAMPLE 2 2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol (compound no. 113)

A solution of 15.8 g of 3-bromopyridine (0.10 mol) in 50 ml of diethyl ether is added dropwise to a mixture of 82 ml of a 1.6M n-butyllithium solution in n-hexane (0.13 mol) under a nitrogen atmosphere at -70° C. The mixture is stirred at -70° C. for 10 minutes and then a solution of 24.7 g of 2-(4-chlorobenzyl)-2-ethylbutanal (0.11 mol) in 50 ml of diethyl ether is added dropwise. After 1 h at -70° C., the mixture is allowed to warm slowly to room temperature and is hydrolyzed with saturated aqueous ammonium chloride solution. The mixture is acidified with dilute hydrochloric acid, and the aqueous phase is separated off and washed with ether and then adjusted to pH 10 to 11 with concentrated ammonia solution while cooling. It is extracted three times with dichloromethane, and the organic phase is dried over Na₂ SO₄ and concentrated. The solid crude product is recrystallized from ethyl acetate/hexane (1:1). 19.2 g (63% of theory) of colorless crystals of melting point 128°-129° C.

Preparation of the starting compound 2-(4-Chlorobenzyl)-2-ethylbutanal

300 ml of toluene, 400 ml of 30 percent (by weight) sodium hydroxide solution and 5.0 g of tetra-n-butylammonium iodide are heated at 80° C. while stirring. To this is slowly added dropwise a mixture of 110 g (1.10 mol) of 2-ethylbutanal and 161 g (1.00 mol) of 4-chlorobenzyl chloride. The mixture is then stirred at 80° C. for 4 h and at room temperature for 14 h, 1,000 ml of toluene are added, and the phases are separated. The organic phase is washed with water, dried over Na₂ SO₄ and concentrated. Fractional distillation results in 123 g (54% of theory) of 2-(4-chlorobenzyl)-2-ethylbutanal as a colorless liquid of boiling point 146°-148° C. at 1 mbar.

The following compounds can also be prepared in a manner corresponding to that in Examples 1 and 2:

                  TABLE 1                                                          ______________________________________                                          ##STR11##                                                                                                         Physical                                   Ex. no.                                                                              A           Ar                data                                       ______________________________________                                         1     C(CH.sub.3)C.sub.2 H.sub.5                                                                 phenyl                                                       2     C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-methylphenyl                                               3     C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-methylphenyl                                               4     C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methylphenyl                                               5     C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3-dimethylphenyl                                           6     C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-dimethylphenyl                                           7     C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,5-dimethylphenyl                                           8     C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,6-dimethylphenyl                                           9     C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-dimethylphenyl                                           10    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-dimethylphenyl                                           11    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,5-trimethylphenyl                                        12    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,6-trimethylphenyl                                        13    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3,5,6-tetramethylphenyl                                    14    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-ethylphenyl                                                15    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-isopropylphenyl                                            16    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-tert.butylphenyl                                           17    C(CH.sub.3)C.sub.2 H.sub.5                                                                 5-indanyl                                                    18    C(CH.sub.3)C.sub.2 H.sub.5                                                                 1-naphthyl                                                   19    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-naphthyl                                                   20    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-methyl-1-naphthyl                                          21    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-biphenyl                                                   22    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-fluorophenyl                                               23    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-fluorophenyl                                               24    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-fluorophenyl                                               25    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3-difluorophenyl                                           26    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-difluorophenyl                                           27    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,5-difluorophenyl                                           28    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,6-difluorophenyl                                           29    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-difluorophenyl                                           30    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-difluorophenyl                                           31    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-fluoro-3-methylphenyl                                      32    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3,5,6-tetrafluorophenyl                                    33    C(CH.sub.3)C.sub.2 H.sub.5                                                                 pentafluorophenyl                                            34    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chlorophenyl                                               35    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-chlorophenyl                                               36    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-chlorophenyl                                               37    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3-dichlorophenyl                                           38    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-dichlorophenyl                                           39    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,5-dichlorophenyl                                           40    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,6-dichlorophenyl                                           41    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-dichlorophenyl                                           42    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-dichlorophenyl                                           43    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,5-trichlorophenyl                                        44    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,6-trichlorophenyl                                        45    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3,6-trichlorophenyl                                        46    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-5-methylphenyl                                      47    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-chloro-4-methylphenyl                                      48    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-4-fluorophenyl                                      49    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-6-fluorophenyl                                      50    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-chloro-2-fluorophenyl                                      51    C(CH.sub.3)C.sub.2 H.sub.5                                                                 pentachlorophenyl                                            52    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-bromophenyl                                                53    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-bromophenyl                                                54    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-bromophenyl                                                55    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-fluoro-4-bromophenyl                                       56    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-trifluoromethylphenyl                                      57    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-trifluoromethylphenyl                                      58    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-trifluoromethylphenyl                                      59    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-bis(trifluoromethyl)-                                                      phenyl                                                       60    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-bis(trifluoromethyl)-                                                      phenyl                                                       61    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-methoxyphenyl                                              62    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-methoxyphenyl                                              63    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methoxyphenyl                                              64    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-dimethoxyphenyl                                          65    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4,5-trimethoxyphenyl                                       66    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-ethoxyphenyl                                               67    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-tetrafluoroethoxyphenyl                                    68    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-trifluoromethoxyphenyl                                     69    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methoxyiminocarbyl-phenyl                                  70    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-ethoxyiminocarbyl-phenyl                                   71    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methoxy-3-methylphenyl                                     72    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-phenoxyphenyl                                              73    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-phenoxyphenyl                                              74    C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               75    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-(4'-chlorophenoxy)-                                                          phenyl)                                                      76    C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-(4'-fluorophenoxy)-                                                          phenyl                                                       77    C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-benzyloxyphenyl                                            78    C(C.sub.2 H.sub.5).sub.2                                                                   phenyl            mp. 130-                                                                       132                                        79    C(C.sub.2 H.sub.5).sub.2                                                                   2-methylphenyl    mp. 92-                                                                        94                                         80    C(C.sub.2 H.sub.5).sub.2                                                                   3-methylphenyl                                               81    C(C.sub.2 H.sub.5).sub.2                                                                   4-methylphenyl    mp. 87-                                                                        88                                         82    C(C.sub.2 H.sub.5).sub.2                                                                   2,3-dimethylphenyl                                           83    C(C.sub.2 H.sub.5).sub.2                                                                   2,4-dimethylphenyl                                           84    C(C.sub.2 H.sub.5).sub.2                                                                   2,5-dimethylphenyl                                           85    C(C.sub.2 H.sub.5).sub.2                                                                   2,6-dimethylphenyl                                           86    C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dimethylphenyl                                           87    C(C.sub.2 H.sub.5).sub.2                                                                   3,5-dimethylphenyl                                           88    C(C.sub.2 H.sub.5).sub.2                                                                   2,4,5-trimethylphenyl                                        89    C(C.sub.2 H.sub.5).sub.2                                                                   2,4,6-trimethylphenyl                                        90    C(C.sub.2 H.sub.5).sub. 2                                                                  2,3,5,6-tetramethylphenyl                                    91    C(C.sub.2 H.sub.5).sub.2                                                                   4-ethylphenyl                                                92    C(C.sub.2 H.sub.5).sub.2                                                                   4-isopropylphenyl                                            93    C(C.sub.2 H.sub.5).sub.2                                                                   4-tert.butylphenyl                                                                               mp. 122-                                                                       124                                        94    C(C.sub.2 H.sub.5).sub.2                                                                   5-indanyl                                                    95    C(C.sub.2 H.sub.5).sub.2                                                                   1-naphthyl        mp. 112-                                                                       113                                        96    C(C.sub.2 H.sub.5).sub.2                                                                   2-naphthyl                                                   97    C(C.sub.2 H.sub.5).sub.2                                                                   2-methyl-1-naphthyl                                          98    C(C.sub.2 H.sub.5).sub.2                                                                   4-biphenyl                                                   99    C(C.sub.2 H.sub.5).sub.2                                                                   2-fluorophenyl                                               100   C(C.sub.2 H.sub.5).sub.2                                                                   3-fluorophenyl    mp. 120-                                                                       122                                        101   C(C.sub.2 H.sub.5).sub.2                                                                   4-fluorophenyl    mp. 148-                                                                       150                                        102   C(C.sub.2 H.sub.5).sub.2                                                                   2,3-difluorophenyl                                           103   C(C.sub.2 H.sub.5).sub.2                                                                   2,4-difluorophenyl                                           104   C(C.sub.2 H.sub.5).sub.2                                                                   2,5-difluorophenyl                                           105   C(C.sub.2 H.sub.5).sub.2                                                                   2,6-difluorophenyl                                           106   C(C.sub.2 H.sub.5).sub.2                                                                   3,4-difluorophenyl                                           107   C(C.sub.2 H.sub.5).sub.2                                                                   3,5-difluorophenyl                                           108   C(C.sub.2 H.sub.5).sub.2                                                                   2-fluoro-3-methylphenyl                                      109   C(C.sub.2 H.sub.5).sub.2                                                                   2,3,5,6-tetrafluorophenyl                                    110   C(C.sub.2 H.sub.5).sub.2                                                                   pentafluorophenyl                                            111   C(C.sub.2 H.sub.5).sub.2                                                                   2-chlorophenyl    mp. 96-                                                                        98                                         112   C(C.sub.2 H.sub.5).sub.2                                                                   3-chlorophenyl                                               113   C(C.sub.2 H.sub.5).sub.2                                                                   4-chlorophenyl    mp. 128-                                                                       129                                        114   C(C.sub.2 H.sub.5).sub.2                                                                   2,3-dichlorophenyl                                           115   C(C.sub.2 H.sub.5).sub.2                                                                   2,4-dichlorophenyl                                                                               mp. 139-                                                                       140                                        116   C(C.sub.2 H.sub.5).sub.2                                                                   2,5-dichlorophenyl                                           117   C(C.sub.2 H.sub.5).sub.2                                                                   2,6-dichlorophenyl                                           118   C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dichlorophenyl                                           119   C(C.sub.2 H.sub.5).sub.2                                                                   3,5-dichlorophenyl                                           120   C(C.sub.2 H.sub.5).sub.2                                                                   2,4,5-trichlorophenyl                                        121   C(C.sub.2 H.sub.5).sub.2                                                                   2,4,6-trichlorophenyl                                        122   C(C.sub.2 H.sub.5).sub.2                                                                   2,3,6-trichlorophenyl                                        123   C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-5-methylphenyl                                      124   C(C.sub.2 H.sub.5).sub.2                                                                   3-chloro-4-methylphenyl                                      125   C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-4-fluorophenyl                                      126   C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-6-fluorophenyl                                      127   C(C.sub.2 H.sub.5).sub.2                                                                   3-chloro-2-fluorophenyl                                      128   C(C.sub.2 H.sub.5).sub.2                                                                   pentachlorophenyl                                            129   C(C.sub.2 H.sub.5).sub.2                                                                   2-bromophenyl                                                130   C(C.sub.2 H.sub.5).sub.2                                                                   3-bromophenyl                                                131   C(C.sub.2 H.sub.5).sub.2                                                                   4-bromophenyl                                                132   C(C.sub.2 H.sub.5).sub.2                                                                   2-fluoro-4-bromophenyl                                       133   C(C.sub.2 H.sub.5).sub.2                                                                   2-trifluoromethylphenyl                                      134   C(C.sub.2 H.sub.5 ).sub.2                                                                  3-trifluoromethylphenyl                                      135   C(C.sub.2 H.sub.5).sub.2                                                                   4-trifluoromethylphenyl                                      136   C(C.sub.2 H.sub.5).sub.2                                                                   2,4-bis(trifluoromethyl)-                                                      phenyl                                                       137   C(C.sub.2 H.sub.5).sub.2                                                                   3,5-bis(trifluoromethyl)-                                                      phenyl                                                       138   C(C.sub.2 H.sub.5).sub.2                                                                   2-methoxyphenyl                                              139   C(C.sub.2 H.sub.5).sub.2                                                                   3-methoxyphenyl                                              140   C(C.sub.2 H.sub.5).sub.2                                                                   4-methoxyphenyl                                              141   C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dimethoxyphenyl                                          142   C(C.sub.2 H.sub.5).sub.2                                                                   3,4,5-trimethoxyphenyl                                       143   C(C.sub.2 H.sub.5).sub.2                                                                   4-ethoxyphenyl                                               144   C(C.sub.2 H.sub.5).sub.2                                                                   4-tetrafluoroethoxyphenyl                                    145   C(C.sub.2 H.sub.5).sub.2                                                                   4-trifluoromethoxyphenyl                                     146   C(C.sub.2 H.sub.5).sub.2                                                                   4-methoxyiminocarbyl-phenyl                                  147   C(C.sub.2 H.sub.5).sub.2                                                                   4-ethoxyiminocarbyl-phenyl                                   148   C(C.sub.2 H.sub.5).sub.2                                                                   4-methoxy-3-methylphenyl                                     149   C(C.sub.2 H.sub.5).sub.2                                                                   3-phenoxyphenyl                                              150   C(C.sub.2 H.sub.5).sub.2                                                                   4-phenoxyphenyl                                              151   C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               152   C(C.sub.2 H.sub.5).sub.2                                                                   4-(4'-chlorophenoxy)-                                                          phenyl)                                                      153   C(C.sub.2 H.sub.5).sub.2                                                                   4-benzyloxyphenyl                                            154   C(CH.sub.2).sub.4                                                                          phenyl                                                       155   C(CH.sub.2).sub.4                                                                          2-methylphenyl                                               156   C(CH.sub.2).sub.4                                                                          3-methylphenyl                                               157   C(CH.sub.2).sub.4                                                                          4-methylphenyl                                               158   C(CH.sub.2).sub.4                                                                          2,3-dimethylphenyl                                           159   C(CH.sub.2).sub.4                                                                          2,4-dimethylphenyl                                           160   C(CH.sub.2).sub.4                                                                          2,5-dimethylphenyl                                           161   C(CH.sub.2).sub.4                                                                          2,6-dimethylphenyl                                           162   C(CH.sub.2).sub.4                                                                          3,4-dimethylphenyl                                           163   C(CH.sub.2).sub.4                                                                          3,5-dimethylphenyl                                           164   C(CH.sub.2).sub.4                                                                          2,4,5-trimethylphenyl                                        165   C(CH.sub.2).sub.4                                                                          2,4,6-trimethylphenyl                                        166   C(CH.sub.2).sub.4                                                                          2,3,5,6-tetramethylphenyl                                    167   C(CH.sub.2).sub.4                                                                          4-ethylphenyl                                                168   C(CH.sub.2).sub.4                                                                          4-isopropylphenyl                                            169   C(CH.sub.2).sub.4                                                                          4-tert.butylphenyl                                           170   C(CH.sub.2).sub.4                                                                          5-indanyl                                                    171   C(CH.sub.2).sub.4                                                                          1-naphthyl                                                   172   C(CH.sub.2).sub.4                                                                          2-naphthyl                                                   173   C(CH.sub.2).sub.4                                                                          2-methyl-1-naphthyl                                          174   C(CH.sub.2).sub.4                                                                          4-biphenyl                                                   175   C(CH.sub.2).sub.4                                                                          2-fluorophenyl    mp. 75-                                                                        76                                         176   C(CH.sub.2).sub.4                                                                          3-fluorophenyl                                               177   C(CH.sub.2).sub.4                                                                          4-fluorophenyl    mp. 166-                                                                       168                                        178   C(CH.sub.2).sub.4                                                                          2,3-difluorophenyl                                           179   C(CH.sub.2).sub.4                                                                          2,4-difluorophenyl                                           180   C(CH.sub.2).sub.4                                                                          2,5-difluorophenyl                                           181   C(CH.sub.2).sub.4                                                                          2,6-difluorophenyl                                           182   C(CH.sub.2).sub.4                                                                          3,4-difluorophenyl                                           183   C(CH.sub.2).sub.4                                                                          3,5-difluorophenyl                                           184   C(CH.sub.2).sub.4                                                                          2-fluoro-3-methylphenyl                                      185   C(CH.sub.2).sub.4                                                                          2,3,5,6-tetrafluorophenyl                                    186   C(CH.sub.2).sub.4                                                                          pentafluorophenyl                                            187   C(CH.sub.2).sub.4                                                                          2-chlorophenyl    mp. 114-                                                                       116                                        188   C(CH.sub.2).sub.4                                                                          3-chlorophenyl                                               189   C(CH.sub.2).sub.4                                                                          4-chlorophenyl    mp. 162-                                                                       164                                        190   C(CH.sub.2).sub.4                                                                          2,3-dichlorophenyl                                           191   C(CH.sub.2).sub.4                                                                          2,4-dichlorophenyl                                                                               mp. 110-                                                                       112                                        192   C(CH.sub.2).sub.4                                                                          2,5-dichlorophenyl                                           193   C(CH.sub.2).sub.4                                                                          2,6-dichlorophenyl                                           194   C(CH.sub.2).sub.4                                                                          3,4-dichlorophenyl                                           195   C(CH.sub.2).sub.4                                                                          3,5-dichlorophenyl                                           196   C(CH.sub.2).sub.4                                                                          2,4,5-trichlorophenyl                                        197   C(CH.sub.2).sub.4                                                                          2,4,6-trichlorophenyl                                        198   C(CH.sub.2).sub.4                                                                          2,3,6-trichlorophenyl                                        199   C(CH.sub.2).sub.4                                                                          2-chloro-5-methylphenyl                                      200   C(CH.sub.2).sub.4                                                                          3-chloro-4-methylphenyl                                      201   C(CH.sub.2).sub.4                                                                          2-chloro-4-fluorophenyl                                      202   C(CH.sub.2).sub.4                                                                          2-chloro-6-fluorophenyl                                      203   C(CH.sub.2).sub.4                                                                          3-chloro-2-fluorophenyl                                      204   C(CH.sub.2).sub.4                                                                          pentachlorophenyl                                            205   C(CH.sub.2).sub.4                                                                          2-bromophenyl                                                206   C(CH.sub.2).sub.4                                                                          3-bromophenyl                                                207   C(CH.sub.2).sub.4                                                                          4-bromophenyl                                                208   C(CH.sub.2).sub.4                                                                          2-fluoro-4-bromophenyl                                       209   C(CH.sub.2).sub.4                                                                          2-trifluoromethylphenyl                                      210   C(CH.sub.2).sub.4                                                                          3-trifluoromethylphenyl                                      211   C(CH.sub.2).sub.4                                                                          4-trifluoromethylphenyl                                      212   C(CH.sub.2).sub.4                                                                          2,4-bis(trifluoromethyl)-                                                      phenyl                                                       213   C(CH.sub.2).sub.4                                                                          3,5-bis(trifluoromethyl)-                                                      phenyl                                                       214   C(CH.sub.2).sub.4                                                                          2-methoxyphenyl                                              215   C(CH.sub.2).sub.4                                                                          3-methoxyphenyl                                              216   C(CH.sub.2).sub.4                                                                          4-methoxyphenyl                                              217   C(CH.sub.2).sub.4                                                                          3,4-dimethoxyphenyl                                          218   C(CH.sub.2).sub.4                                                                          3,4,5-trimethoxyphenyl                                       219   C(CH.sub.2).sub.4                                                                          4-ethoxyphenyl                                               220   C(CH.sub. 2).sub.4                                                                         4-tetrafluoroethoxyphenyl                                    221   C(CH.sub.2).sub.4                                                                          4-trifluoromethoxyphenyl                                     222   C(CH.sub.2).sub.4                                                                          4-methoxyiminocarbyl-phenyl                                  223   C(CH.sub.2).sub.4                                                                          4-ethoxyiminocarbyl-phenyl                                   224   C(CH.sub.2).sub.4                                                                          4-methoxy-3-methylphenyl                                     225   C(CH.sub.2).sub.4                                                                          3-phenoxyphenyl                                              226   C(CH.sub.2).sub.4                                                                          4-phenoxyphenyl                                              227   C(CH.sub.2).sub.4                                                                          2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               228   C(CH.sub.2).sub.4                                                                          3-(4'-fluorophenoxy)-                                                          phenyl                                                       229   C(CH.sub.2).sub.4                                                                          4-benzyloxyphenyl                                            230   C(CH.sub.2).sub.5                                                                          phenyl            mp. 117-                                                                       119                                        231   C(CH.sub.2).sub.5                                                                          2-methylphenyl                                               232   C(CH.sub.2).sub.5                                                                          3-methylphenyl                                               233   C(CH.sub.2).sub.5                                                                          4-methylphenyl                                               234   C(CH.sub.2).sub.5                                                                          2,3-dimethylphenyl                                           235   C(CH.sub.2).sub.5                                                                          2,4-dimethylphenyl                                           236   C(CH.sub.2).sub.5                                                                          2,5-dimethylphenyl                                           237   C(CH.sub.2).sub.5                                                                          2,6-dimethylphenyl                                           238   C(CH.sub.2).sub.5                                                                          3,4-dimethylphenyl                                           239   C(CH.sub.2).sub.5                                                                          3,5-dimethylphenyl                                           240   C(CH.sub.2).sub.5                                                                          2,4,5-trimethylphenyl                                        241   C(CH.sub.2).sub.5                                                                          2,4,6-trimethylphenyl                                        242   C(CH.sub.2).sub.5                                                                          2,3,5,6-tetramethylphenyl                                    243   C(CH.sub.2).sub.5                                                                          4-ethylphenyl                                                244   C(CH.sub.2).sub.5                                                                          4-isopropylphenyl                                            245   C(CH.sub.2).sub.5                                                                          4-tert-butylphenyl                                           246   C(CH.sub.2).sub.5                                                                          5-indanyl                                                    247   C(CH.sub.2).sub.5                                                                          1-naphthyl                                                   248   C(CH.sub.2).sub.5                                                                          2-naphthyl                                                   249   C(CH.sub.2).sub.5                                                                          2-methyl-1-naphthyl                                          250   C(CH.sub.2).sub.5                                                                          4-biphenyl                                                   251   C(CH.sub.2).sub.5                                                                          2-fluorophenyl    mp. 146-                                                                       148                                        252   C(CH.sub.2).sub.5                                                                          3-fluorophenyl    mp. 132-                                                                       134                                        253   C(CH.sub.2).sub.5                                                                          4-fluorophenyl    mp. 126-                                                                       127                                        254   C(CH.sub.2).sub.5                                                                          2,3-difluorophenyl                                           255   C(CH.sub.2).sub.5                                                                          2,4-difluorophenyl                                           256   C(CH.sub.2).sub.5                                                                          2,5-difluorophenyl                                           257   C(CH.sub.2).sub.5                                                                          2,6-difluorophenyl                                           258   C(CH.sub.2).sub.5                                                                          3,4-difluorophenyl                                           259   C(CH.sub.2).sub.5                                                                          3,5-difluorophenyl                                           260   C(CH.sub.2).sub.5                                                                          2-fluoro-3-methylphenyl                                      261   C(CH.sub.2).sub.5                                                                          2,3,5,6-tetrafluorophenyl                                    262   C(CH.sub.2).sub.5                                                                          pentafluorphenyl                                             263   C(CH.sub.2).sub.5                                                                          2-chlorophenyl    mp. 162-                                                                       164                                        264   C(CH.sub.2).sub.5                                                                          3-chlorophenyl                                               265   C(CH.sub.2).sub.5                                                                          4-chlorophenyl    mp. 155-                                                                       156                                        266   C(CH.sub.2).sub.5                                                                          2,3-dichlorophenyl                                           267   C(CH.sub.2).sub.5                                                                          2,4-dichlorophenyl                                                                               oil;                                                                           N-oxide                                                                        mp. 205-                                                                       207                                        268   C(CH.sub.2).sub.5                                                                          2,5-dichlorophenyl                                           269   C(CH.sub.2).sub.5                                                                          2,6-dichlorophenyl                                           270   C(CH.sub.2).sub.5                                                                          3,4-dichlorophenyl                                                                               mp. 181-                                                                       183                                        271   C(CH.sub.2).sub.5                                                                          3,5-dichlorophenyl                                           272   C(CH.sub.2).sub.5                                                                          2,4,5-trichlorophenyl                                        273   C(CH.sub.2).sub.5                                                                          2,4,6-trichlorophenyl                                        274   C(CH.sub.2).sub.5                                                                          2,3,6-trichlorophenyl                                        275   C(CH.sub.2).sub.5                                                                          2-chloro-5-methylphenyl                                      276   C(CH.sub.2).sub.5                                                                          3-chloro-4-methylphenyl                                      277   C(CH.sub.2).sub.5                                                                          2-chloro-4-fluorophenyl                                      278   C(CH.sub.2).sub.5                                                                          2-chloro-6-fluorophenyl                                      279   C(CH.sub.2).sub.5                                                                          3-chloro-2-fluorophenyl                                      280   C(CH.sub.2).sub.5                                                                          pentachlorophenyl                                            281   C(CH.sub.2).sub.5                                                                          2-bromophenyl                                                282   C(CH.sub.2).sub.5                                                                          3-bromophenyl                                                283   C(CH.sub.2).sub.5                                                                          4-bromophenyl     mp. 190-                                                                       191                                        284   C(CH.sub.2).sub.5                                                                          2-fluoro-4-bromophenyl                                       285   C(CH.sub.2).sub.5                                                                          2-trifluoromethylphenyl                                      286   C(CH.sub.2).sub.5                                                                          3-trifluoromethylphenyl                                      287   C(CH.sub.2).sub.5                                                                          4-trifluoromethylphenyl                                      288   C(CH.sub.2).sub.5                                                                          2,4-bis(trifluoromethyl)-                                                      phenyl                                                       289   C(CH.sub.2).sub.5                                                                          3,5-bis(trifluoromethyl)-                                                      phenyl                                                       290   C(CH.sub.2).sub.5                                                                          2-methoxyphenyl                                              291   C(CH.sub.2).sub.5                                                                          3-methoxyphenyl                                              292   C(CH.sub.2).sub.5                                                                          4-methoxyphenyl                                              293   C(CH.sub.2).sub.5                                                                          3,4-dimethoxyphenyl                                          294   C(CH.sub.2).sub.5                                                                          3,4,5-trimethoxyphenyl                                       295   C(CH.sub.2).sub.5                                                                          4-ethoxyphenyl                                               296   C(CH.sub.2).sub.5                                                                          4-tetrafluoroethoxyphenyl                                    297   C(CH.sub.2).sub.5                                                                          4-trifluoromethoxyphenyl                                     298   C(CH.sub.2).sub.5                                                                          4-methoxyiminocarbyl-phenyl                                  299   C(CH.sub.2).sub.5                                                                          4-ethoxyiminocarbyl-phenyl                                   300   C(CH.sub.2).sub.5                                                                          4-methoxy-3-methylphenyl                                     301   C(CH.sub.2).sub.5                                                                          3-phenoxyphenyl                                              302   C(CH.sub.2).sub.5                                                                          4-phenoxyphenyl                                              303   C(CH.sub.2).sub.5                                                                          2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               304   C(CH.sub.2).sub.5                                                                          3-(4'-fluorophenoxy)-                                                          phenyl                                                       305   C(CH.sub.2).sub.5                                                                          4-benzyloxyphenyl                                            306   C(CH.sub.3)nC.sub.3 H.sub.7                                                                phenyl            oil;                                                                           N-oxide                                                                        mp. 154-                                                                       156                                        307   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-methylphenyl                                               308   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-methylphenyl                                               309   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-methylphenyl                                               310   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3-dimethylphenyl                                           311   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-dimethylphenyl                                           312   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,5-dimethylphenyl                                           313   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,6-dimethylphenyl                                           314   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-dimethylphenyl                                           315   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-dimethylphenyl                                           316   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4,5-trimethylphenyl                                        317   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4,6-trimethylphenyl                                        318   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3,5,6-tetramethylphenyl                                    319   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-ethylphenyl                                                320   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-isopropylphenyl                                            321   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-tert.butylphenyl                                           322   C(CH.sub.3)nC.sub.3 H.sub.7                                                                5-indanyl                                                    323   C(CH.sub.3)nC.sub.3 H.sub.7                                                                1-naphthyl                                                   324   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-naphthyl                                                   325   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-methyl-1-naphthyl                                          326   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-biphenyl                                                   327   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-fluorophenyl                                               328   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-fluorophenyl                                               329   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-fluorophenyl                                               330   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3-difluorophenyl                                           331   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-difluorophenyl                                           332   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,5-difluorophenyl                                           333   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,6-difluorophenyl                                           334   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-difluorophenyl                                           335   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-difluorophenyl                                           336   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-fluoro-3-methylphenyl                                      337   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3,5,6-tetrafluorophenyl                                    338   C(CH.sub.3)nC.sub.3 H.sub.7                                                                pentafluorophenyl                                            339   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chlorophenyl                                               340   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-chlorophenyl                                               341   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-chlorophenyl    oil;                                                                           N-oxide:                                                                       mp. 159-                                                                       160                                        342   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3-dichlorophenyl                                           343   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-dichlorophenyl                                           344   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,5-dichlorophenyl                                           345   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,6-dichlorophenyl                                           346   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-dichlorophenyl                                           347   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-dichlorophenyl                                           348   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4,5-trichlorophenyl                                        349   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4,6-trichlorophenyl                                        350   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3,6-trichlorophenyl                                        351   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-5-methylphenyl                                      352   C(CH.sub. 3)nC.sub.3 H.sub.7                                                               3-chloro-4-methylphenyl                                      353   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-4-fluorophenyl                                      354   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-6-fluorophenyl                                      355   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-chloro-2-fluorophenyl                                      356   C(CH.sub.3)nC.sub.3 H.sub.7                                                                pentachlorophenyl                                            357   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-bromophenyl                                                358   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-bromophenyl                                                359   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-bromophenyl                                                360   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-fluoro-4-bromophenyl                                       361   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-trifluoromethylphenyl                                      362   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-trifluoromethylphenyl                                      363   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-trifluoromethylphenyl                                      364   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-bis(trifluoromethyl)-                                                      phenyl                                                       365   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-bis(trifluoromethyl)-                                                      phenyl                                                       366   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-methoxyphenyl                                              367   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-methoxyphenyl                                              368   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-methoxyphenyl                                              369   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-dimethoxyphenyl                                          370   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4,5-trimethoxyphenyl                                       371   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-ethoxyphenyl                                               372   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-tetrafluoroethoxyphenyl                                    373   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-trifluoromethoxyphenyl                                     374   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-methoxyiminocarbyl-phenyl                                  375   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-ethoxyiminocarbyl-phenyl                                   376   C(CH.sub.3)nC.sub. 3 H.sub.7                                                               4-methoxy-3-methylphenyl                                     377   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-phenoxyphenyl                                              378   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-phenoxyphenyl                                              379   C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               380   C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-(4'-fluorophenoxy)-                                                          phenyl                                                       381   C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-benzyloxyphenyl                                            382   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         phenyl            oil                                        383   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-methylphenyl                                               384   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-methylphenyl                                               385   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methylphenyl                                               386   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3-dimethylphenyl                                           387   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4-dimethylphenyl                                           388   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,5-dimethylphenyl                                           389   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,6-dimethylphenyl                                           390   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-dimethylphenyl                                           391   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-dimethylphenyl                                           392   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,5-trimethylphenyl                                        393   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,6-trimethylphenyl                                        394   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3,5,6-tetramethylphenyl                                    395   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-ethylphenyl                                                396   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-isopropylphenyl                                            397   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-tert.butylphenyl                                           398   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         5-indanyl                                                    399   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         1-naphthyl                                                   400   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-naphthyl                                                   401   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-methyl-1-napthyl                                           402   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-biphenyl                                                   403   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-fluorophenyl                                               404   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-fluorophenyl                                               405   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-fluorophenyl                                               406   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3-difluorophenyl                                           407   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4-difluorophenyl                                           408   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,5-difluorophenyl                                           409   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,6-difluorophenyl                                           410   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-difluorophenyl                                           411   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-difluorophenyl                                           412   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-fluoro-3-methylphenyl                                      413   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3,5,6-tetrafluorophenyl                                    414   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         pentafluorophenyl                                            415   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chlorophenyl                                               416   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-chlorophenyl                                               417   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-chlorophenyl                                               418   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3-dichlorophenyl                                           419   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4-dichlorophenyl                                           420   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,5-dichlorophenyl                                           421   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,6-dichlorophenyl                                           422   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-dichlorophenyl                                           423   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-dichlorophenyl                                           424   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,5-trichlorophenyl                                        425   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,6-trichlorophenyl                                        426   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3,6-trichlorophenyl                                        427   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chloro-5-methylphenyl                                      428   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-chloro-4-methylphenyl                                      429   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chloro-4-fluorophenyl                                      430   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chloro-6-fluorophenyl                                      431   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-chloro-2-fluorophenyl                                      432   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         pentachlorophenyl                                            433   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-bromophenyl                                                434   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-bromophenyl                                                435   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-bromophenyl                                                436   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-fluoro-4-bromophenyl                                       437   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-trifluoromethylphenyl                                      438   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-trifluoromethylphenyl                                      439   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-trifluormethylphenyl                                       440   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4-bis(trifluoromethyl)-                                                      phenyl                                                       441   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-bis(trifluoromethyl)-                                                      phenyl                                                       442   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-methoxyphenyl                                              443   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-methoxyphenyl                                              444   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methoxyphenyl                                              445   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-dimethoxyphenyl                                          446   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4,5-trimethoxyphenyl                                       447   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-ethoxyphenyl                                               448   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-tetrafluoroethoxyphenyl                                    449   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-trifluoromethoxyphenyl                                     450   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methoxyiminocarbyl-phenyl                                  451   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-ethoxyiminocarbyl-phenyl                                   452   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methoxy-3-methylphenyl                                     453   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-phenoxyphenyl                                              454   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-phenoxyphenyl                                              455   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               456   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-(4'-fluorophenoxy)-                                                          phenyl                                                       457   C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-benzyloxyphenyl                                            458   C(CH.sub.2).sub.3 OCH.sub.2                                                                phenyl                                                       459   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-methylphenyl                                               460   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-methylphenyl                                               461   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methylphenyl                                               462   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3-dimethylphenyl                                           463   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-dimethylphenyl                                           464   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,5-dimethylphenyl                                           465   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,6-dimethylphenyl                                           466   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-dimethylphenyl                                           467   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-dimethylphenyl                                           468   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4,5-trimethylphenyl                                        469   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4,6-trimethylphenyl                                        470   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3,5,6-tetramethylphenyl                                    471   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-ethylphenyl                                                472   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-isopropylphenyl                                            473   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-tert.butylphenyl                                           474   C(CH.sub.2).sub.3 OCH.sub.2                                                                5-indanyl                                                    475   C(CH.sub.2).sub.3 OCH.sub.2                                                                1-naphthyl                                                   476   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-naphthyl                                                   477   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-methyl-1-napthyl                                           478   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-biphenyl                                                   479   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-fluorophenyl                                               480   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-fluorophenyl                                               481   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-fluorophenyl                                               482   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3-difluorophenyl                                           483   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-difluorophenyl                                           484   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,5-difluorophenyl                                           485   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,6-difluorophenyl                                           486   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-difluorophenyl                                           487   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-difluorophenyl                                           488   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-fluoro-3-methylphenyl                                      489   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3,5,6-tetrafluorophenyl                                    490   C(CH.sub.2).sub.3 OCH.sub.2                                                                pentafluorophenyl                                            491   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chlorophenyl                                               492   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-chlorophenyl                                               493   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-chlorophenyl                                               494   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3-dichlorophenyl                                           495   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-dichlorophenyl                                           496   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,5-dichlorophenyl                                           497   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,6-dichlorophenyl                                           498   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-dichlorophenyl                                           499   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-dichlorophenyl                                           500   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4,5-trichlorophenyl                                        501   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4,6-trichlorophenyl                                        502   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3,6-trichlorophenyl                                        503   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-5-methylphenyl                                      504   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-chloro-4-methylphenyl                                      505   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-4-fluorophenyl                                      506   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-6-fluorophenyl                                      507   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-chloro-2-fluorophenyl                                      508   C(CH.sub.2).sub.3 OCH.sub.2                                                                pentachlorophenyl                                            509   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-bromophenyl                                                510   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-bromophenyl                                                511   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-bromophenyl                                                512   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-fluoro-4-bromophenyl                                       513   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-trifluoromethylphenyl                                      514   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-trifluoromethylphenyl                                      515   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-trifluoromethylphenyl                                      516   C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-bis(trifluoromethyl)-                                                      phenyl                                                       517   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-bis(trifluoromethyl)-                                                      phenyl                                                       518   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-methoxyphenyl                                              519   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-methoxyphenyl                                              520   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methoxyphenyl                                              521   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-dimethoxyphenyl                                          522   C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4,5-trimethoxyphenyl                                       523   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-ethoxyphenyl                                               524   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-tetrafluoroethoxyphenyl                                    525   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-trifluoromethoxyphenyl                                     526   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methoxyiminocarbyl-phenyl                                  527   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-ethoxyiminocarbyl-phenyl                                   528   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methoxy-3-methylphenyl                                     529   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-phenoxyphenyl                                              530   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-phenoxyphenyl                                              531   C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               532   C(CH.sub.2).sub.3 OCH.sub.2                                                                3-(4'-fluorophenoxy)-                                                          phenyl                                                       533   C(CH.sub.2).sub.3 OCH.sub.2                                                                4-benzyloxyphenyl                                            534   C(CH.sub.2).sub.2                                                                          phenyl                                                       535   C(CH.sub.2).sub.2                                                                          2-methylphenyl                                               536   C(CH.sub.2).sub.2                                                                          3-methylphenyl                                               537   C(CH.sub.2).sub.2                                                                          4-methylphenyl                                               538   C(CH.sub.2).sub.2                                                                          2,3-dimethylphenyl                                           539   C(CH.sub.2).sub.2                                                                          2,4-dimethylphenyl                                           540   C(CH.sub.2).sub.2                                                                          2,5-dimethylphenyl                                           541   C(CH.sub.2).sub.2                                                                          2,6-dimethylphenyl                                           542   C(CH.sub.2).sub.2                                                                          3,4-dimethylphenyl                                           543   C(CH.sub.2).sub.2                                                                          3,5-dimethylphenyl                                           544   C(CH.sub.2).sub.2                                                                          2,4,5-trimethylphenyl                                        545   C(CH.sub.2).sub.2                                                                          2,4,6-trimethylphenyl                                        546   C(CH.sub.2).sub.2                                                                          2,3,5,6-tetramethylphenyl                                    547   C(CH.sub.2).sub.2                                                                          4-ethylphenyl                                                548   C(CH.sub.2).sub.2                                                                          4-isopropylphenyl                                            549   C(CH.sub.2).sub.2                                                                          4-tert.butylphenyl                                           550   C(CH.sub.2).sub.2                                                                          5-indanyl                                                    551   C(CH.sub.2).sub.2                                                                          1-naphthyl                                                   552   C(CH.sub.2).sub.2                                                                          2-naphthyl                                                   553   C(CH.sub.2).sub.2                                                                          2-methyl-1-napthyl                                           554   C(CH.sub.2).sub.2                                                                          4-biphenyl                                                   555   C(CH.sub.2).sub.2                                                                          2-fluorophenyl                                               556   C(CH.sub.2).sub.2                                                                          3-fluorophenyl                                               557   C(CH.sub.2).sub.2                                                                          4-fluorophenyl                                               558   C(CH.sub.2).sub.2                                                                          2,3-difluorophenyl                                           559   C(CH.sub.2).sub.2                                                                          2,4-difluorophenyl                                           560   C(CH.sub.2).sub.2                                                                          2,5-difluorophenyl                                           561   C(CH.sub.2).sub.2                                                                          2,6-difluorophenyl                                           562   C(CH.sub.2).sub.2                                                                          3,4-difluorophenyl                                           563   C(CH.sub.2).sub.2                                                                          3,5-difluorophenyl                                           564   C(CH.sub.2).sub.2                                                                          2-fluoro-3-methylphenyl                                      565   C(CH.sub.2).sub.2                                                                          2,3,5,6-tetrafluorophenyl                                    566   C(CH.sub.2).sub.2                                                                          pentafluorophenyl                                            567   C(CH.sub.2).sub.2                                                                          2-chlorophenyl                                               568   C(CH.sub.2).sub.2                                                                          3-chlorophenyl                                               569   C(CH.sub.2).sub.2                                                                          4-chlorophenyl                                               570   C(CH.sub.2).sub.2                                                                          2,3-dichlorophenyl                                           571   C(CH.sub.2).sub.2                                                                          2,4-dichlorophenyl                                           572   C(CH.sub.2).sub.2                                                                          2,5-dichlorophenyl                                           573   C(CH.sub.2).sub.2                                                                          2,6-dichlorophenyl                                           574   C(CH.sub.2).sub.2                                                                          3,4-dichlorophenyl                                           575   C(CH.sub.2).sub.2                                                                          3,5-dichlorophenyl                                           576   C(CH.sub.2).sub.2                                                                          2,4,5-trichlorophenyl                                        577   C(CH.sub.2).sub.2                                                                          2,4,6-trichlorophenyl                                        578   C(CH.sub.2).sub.2                                                                          2,3,6-trichlorophenyl                                        579   C(CH.sub.2).sub.2                                                                          2-chloro-5-methylphenyl                                      580   C(CH.sub.2).sub.2                                                                          3-chloro-4-methylphenyl                                      581   C(CH.sub.2).sub.2                                                                          2-chloro-4-fluorophenyl                                      582   C(CH.sub.2).sub.2                                                                          2-chloro-6-fluorophenyl                                      583   C(CH.sub.2).sub.2                                                                          3-chloro-2-fluorophenyl                                      584   C(CH.sub.2).sub.2                                                                          pentachlorophenyl                                            585   C(CH.sub.2).sub.2                                                                          2-bromophenyl                                                586   C(CH.sub.2).sub.2                                                                          3-bromophenyl                                                587   C(CH.sub.2).sub.2                                                                          4-bromophenyl                                                588   C(CH.sub.2).sub.2                                                                          2-fluoro-4-bromophenyl                                       589   C(CH.sub.2).sub.2                                                                          2-trifluoromethylphenyl                                      590   C(CH.sub.2).sub.2                                                                          3-trifluoromethylphenyl                                      591   C(CH.sub.2).sub.2                                                                          4-trifluoromethylphenyl                                      592   C(CH.sub.2 ).sub.2                                                                         2,4-bis(trifluoromethyl)-                                                      phenyl                                                       593   C(CH.sub.2).sub.2                                                                          3,5-bis(trifluoromethyl)-                                                      phenyl                                                       594   C(CH.sub.2).sub.2                                                                          2-methoxyphenyl                                              595   C(CH.sub.2).sub.2                                                                          3-methoxyphenyl                                              596   C(CH.sub.2).sub.2                                                                          4-methoxyphenyl                                              597   C(CH.sub.2).sub.2                                                                          3,4-dimethoxyphenyl                                          598   C(CH.sub.2).sub.2                                                                          3,4,5-trimethoxyphenyl                                       599   C(CH.sub.2).sub.2                                                                          4-ethoxyphenyl                                               600   C(CH.sub.2).sub.2                                                                          4-tetrafluoroethoxyphenyl                                    601   C(CH.sub.2).sub.2                                                                          4-trifluoromethoxyphenyl                                     602   C(CH.sub.2).sub.2                                                                          4-methoxyiminocarbyl-phenyl                                  603   C(CH.sub.2).sub.2                                                                          4-ethoxyiminocarbyl-phenyl                                   604   C(CH.sub.2).sub.2                                                                          4-methoxy-3-methylphenyl                                     605   C(CH.sub.2).sub.2                                                                          3-phenoxyphenyl                                              606   C(CH.sub.2).sub.2                                                                          4-phenoxyphenyl                                              607   C(CH.sub.2).sub.2                                                                          2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                               608   C(CH.sub.2).sub.2                                                                          3-(4'-fluorophenoxy)-                                                          phenyl                                                       609   C(CH.sub.2).sub.2                                                                          4-benzyloxyphenyl                                            ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR12##                                                                     Ex.                                                                            no.  R.sup.2                                                                               A           Ar          Physical data                              ______________________________________                                         610  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   phenyl      oil                                        611  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-chlorophenyl                                                                             oil                                        612  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-fluorophenyl                                                                             oil                                        613  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2,4-dichlorophenyl                                                                         oil                                        614  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2-methylphenyl                                         615  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-methylphenyl                                         616  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-tert.-butylphenyl                                    617  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2-naphthyl                                             618  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2-fluorophenyl                                         619  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-bromophenyl                                          620  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   3-fluorophenyl                                         621  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dichlorophenyl                                     622  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          phenyl                                                 623  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-methylphenyl                                         624  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-methylphenyl                                         625  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-tert.-butylphenyl                                    626  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-naphthyl                                             627  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-fluorophenyl                                         628  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          3-fluorophenyl                                         629  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-fluorophenyl                                         630  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-bromophenyl                                          631  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-chlorophenyl                                         632  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-chlorophenyl                                         633  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2,4-dichlorophenyl                                     634  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          3,4-dichlorophenyl                                     635  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          phenyl                                                 636  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-methylphenyl                                         637  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-methylphenyl                                         638  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-tert.-butylphenyl                                    639  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-naphthyl                                             640  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-fluorophenyl                                         641  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          3-fluorophenyl                                         642  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-fluorophenyl                                         643  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-bromophenyl                                          644  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-chlorophenyl                                         645  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-chlorophenyl                                         646  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2,4-dichlorophenyl                                     647  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          3,4-dichlorophenyl                                     648  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   phenyl                                                 649  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2-methylphenyl                                         650  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-methylphenyl                                         651  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-tert.-butylphenyl                                    652  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2-naphthyl                                             653  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2-fluorophenyl                                         654  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   3-fluorophenyl                                         655  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-fluorophenyl                                         656  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-bromophenyl                                          657  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-chlorophenyl                                         658  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2,4-dichlorophenyl                                     659  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   3,4-dichlorophenyl                                     660  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-biphenyl                                             ______________________________________                                    

Generally speaking, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the Ascomycetes and Basidiomycetes classes. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia species in cotton and lawns,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in vegetables and fruit.

The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi, or the plants, seed, materials or soil to be protected against fungus attack are treated with a fungicidally effective amount of the active ingredient.

The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose.

The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials (wood), for example against Paecilomyces variotii.

When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 10, g are generally used per kg of seed.

The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. 90 parts by weight of compound no. 230 (Table 1) is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 306 (Table 1) is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

III. 20 parts by weight of compound no. 341 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.

IV. 20 parts by weight of compound no. 382 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

V. 80 parts by weight of compound no. 175 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained.

VI. 3 parts by weight of compound no. 187 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of compound no. 191 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 40 parts by weight of compound no. 253 is intimately mixed with 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in water gives an aqueous dispersion.

IX. 20 parts by weight of compound no. 267 is intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

USE EXAMPLES

For comparison purposes, the compound 3-phenyl-2,2-dimethyl-1-(3-pyridyl)propan-1-ol (A) disclosed in EP 302,365 was used.

USE EXAMPLE 1

Action on Botrytis cinerea in pimientos

Pimiento seedlings of the "Neusiedler Ideal Elite" variety with 4 to 5 well developed leaves were sprayed to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprayed with a conidial suspension of the fungus Botrytis cinerea and kept in a high-humidity chamber at 22° to 24° C. After 5 days, the disease had spread on the untreated control plants to such an extent that the necroses covered the major portion of the leaves. The leaf attack was assessed.

The results show that active ingredients 230, 306, 341 and 382, applied as 0.05% spray liquors, have a better fungicidal action (90%) than prior art active ingredient A (55%).

USE EXAMPLE 2

Action on Pyrenophora teres

Barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions consisting (dry basis) of 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres, and set up for 48 hours in a high-humidity climatic cabinet at 18° C. The plants were then cultivated for a further 5 days in the greenhouse at 20° to 22° C. and a relative humidity of 70° C. The extent of fungus spread was then assessed.

The results show that active ingredients 175, 187, 191, 253, 267, 306, 341 and 382, applied as 0.025% spray liquors, have a better fungicidal action (98%) than prior art active ingredient A (60%). 

We claim:
 1. A pyridine compound having the following formula: ##STR13## where R¹ is hydrogen; A is one of the groups ##STR14## where R³ and R⁴ are identical or differ and each is C₁ -C₆ -alkyl, with the proviso that R³ and R⁴ are not simultaneously methyl; R⁵ is one of the groups (CH₂)_(n), n denoting 1, 2, 3, 4 or 5; Ar is phenyl which is unsubstituted or bears from one to five substituents selected from the group consisting of C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.
 2. A fungicidal composition containing a carrier and a fungicidally effective amount of a pyridine compound of the formula ##STR15## where R¹ is hydrogen; A is one of the groups ##STR16## where R³ and R⁴ are identical or differ and each is C₁ -C₆ -alkyl, with the proviso that R³ and R⁴ are not simultaneously methyl; R⁵ is one of the groups (CH₂)_(n), n denoting 1, 2, 3, 4 or 5; Ar is phenyl which is unsubstituted or bears from one to five substituents selected from the group consisting of C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.
 3. A method for combating fungi, wherein the fungi, or the materials, plants, soils or seed threatened by fungus attack are treated with a fungicidally effective amount of a pyridine compound of the formula ##STR17## where R¹ is hydrogen; A is one of the groups ##STR18## where R³ and R⁴ are identical or differ and each is C₁ -C₆ -alkyl, with the proviso that R³ and R⁴ are not simultaneously methyl; R⁵ is one of the groups (CH₂)_(n), n denoting 1, 2, 3, 4 or 5; Ar is phenyl which is unsubstituted or bears from one to five substituents selected from the group consisting of C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.
 4. A compound of the formula 1 as set forth in claim 1, R¹ denoting hydrogen, A being C(CH₂)₅ and Ar being phenyl.
 5. A compound of the formula 1 as set forth in claim 1, R¹ denoting hydrogen, A being C(CH₃)nC₃ H₇ and Ar being phenyl.
 6. A compound of the formula 1 as set forth in claim 1, R¹ denoting hydrogen, A being C(CH₃)nC₃ H₇ and Ar being 4-chlorophenyl.
 7. A compound of the formula 1 as set forth in claim 1, R¹ denoting hydrogen, A being C(C₂ H₅)nC₄ H₉ and Ar being phenyl.
 8. A compound of the formula 1 as set forth in claim 1, R¹ denoting hydrogen, A being C(CH₂)₄ and Ar being 4-fluorophenyl. 